


Playing Nice

by goldenraeofsun



Category: Supernatural
Genre: Dean Winchester Has Self-Worth Issues, Enemies to Friends to Lovers, Enemies to Lovers, Fluff, Loner Castiel (Supernatural), M/M, Nerd Dean Winchester, Snowed In, Trapped
Language: English
Status: Completed
Published: 2021-02-24
Updated: 2021-02-24
Packaged: 2021-03-15 03:42:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,610
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29677902
Author URL: https://archiveofourown.org/users/goldenraeofsun/pseuds/goldenraeofsun
Summary: Dean can't believe Charlie kicked him out of her birthday game night extravaganza and trapped him upstairs with Castiel, the jackass who thinks he's too good to slum it with the rest of them at Happy Hour. Sure, Dean might have taken his Monopoly losses too far, and Castiel definitely cheated at Settlers of Catan, but why did they have to be in time outtogether?
Relationships: Castiel/Dean Winchester
Comments: 49
Kudos: 251





	Playing Nice

**Author's Note:**

> Thanks to [inloveiwthsaturn](https://inlovewithsaturn.tumblr.com/) for the beta read!

**Hour -4**

Dean stomps his feet on the mat, trying to get rid of the snow caking stubbornly to his boots. It was a two minute walk from where he carefully parked his baby several cars down the driveway of Charlie’s rented cabin, but Dean and Sam look like they’d gone toe to toe with an avalanche. As the door opens, grins. “Did someone say video games?” 

Charlie beams as she accepts a hello hug from Sam. “Just in time!” she says, tugging them inside. “Kevin and Garth got here ten minutes ago. Jo’s making a liquor run, and Castiel is finishing setting up Monopoly.”

Dean’s relieved grin at finally getting out of the cold falls off his face at Castiel’s name. “Seriously?”

“It’s a legit game,” Charlie chides as she directs them further into the luxurious cabin she and the rest of her birthday party guests rented for the long weekend, “more legit than Vampirates vs. Goulpires, at any rate,” she mutters under her breath. Before Dean could defend his _totally not made up RPG,_ she adds, “Anyway, he also brought Clue, Sorry, Uno, and Settlers of Catan, before you jump down his throat for Monopoly.”

Dean scowls but admits, “I guess it wouldn’t be game night without the rest.”

“Exactly,” Charlie says primly.

“Nice place,” Sam says, unravelling his scarf as he walks inside, marveling at the exposed wood and other home deco shit Dean couldn’t care less about. There aren’t creepy paintings with eyes that follow you around or mounted animal heads on the wall, so it’s all good in Dean’s book. The owners are people who probably go _glamping_.

“It was a steal at this time of the year,” Charlie says with a grin. “Who knew nobody wanted to freeze their asses off in the middle of nowhere in January?”

“Wifi?” Sam asks, already hopefully rooting around in his pocket for his phone.

“I didn’t ask,” Charlie says cheerfully. As Sam’s face falls, she swats him in the arm. “This is going to be a completely offline weekend - and that’s coming from _me_. Don’t be a baby about it.” 

Just before the threshold of the living room, Charlie tugs Dean off to the side. “Hey, wait a sec.” They listen for a second as Sam’s appearance causes a brief uproar in loud greetings. “I know you don’t like Castiel-”

“’Cause he’s a dick,” Dean shoots back automatically.

“-but play nice,” Charlie continues, rolling her eyes. “It’s my birthday, and we definitely don’t need any macho man contests, got it?”

“Got it,” Dean grumbles. “But-”

“What?”

“I’m not gonna be blamed if he starts it,” Dean says, and he would cross his arms across his chest if he wasn’t carrying two bags full of three extra controllers and six videogames. He settles for glaring down at Charlie imperiously since he’s got the height advantage.

“See,” Charlie rolls her eyes, “This is why I’m so glad I’m a lesbian.”

**Hour -3**

“Come on!” Dean howls as Castiel fishes out the wad of wedged bills from underneath Free Parking. “He’s already bought half the board!”

Charlie looks up from reorganizing the bank’s haphazard stacks of ones, fives, tens, twenties, and fifties next to a pathetic pair of two five-hundred bills. The rest are already owned by Castiel.

Sam elbows him in the ribs. “Play nice,” he hisses. Easy for him to say, since he’d already given up and declared bankruptcy twenty minutes ago. With one final glare, Sam turns back to the poker game at the other end of the table. By the looks of things, Jo has everything well under control.

“He started it,” Dean retorts right to Castiel’s smirking face.

“By winning?” Castiel asks in an innocent tone that doesn’t fool Dean at all.

“By being an asshole,” Dean says darkly.

Sam elbows him again.

Charlie rolls her eyes.

**Hour -2.5**

“You can’t cut the guy some slack?” Sam asks disapprovingly from behind him.

Dean scowls and adds another splash of whiskey to his glass. Thank god Charlie called a ten minute break to drink up, hit the head, and make out with your hot girlfriend. The last one only applied to Charlie and Dorothy, since Dean and Sam were both painfully single, Kevin was focusing on his Masters’ degree, Garth left Bess back home, and Jo broke up with her last girlfriend last week. 

Castiel, of course, has never brought along any girlfriend to Charlie’s gatherings and is notoriously private. He’s never mentioned a girlfriend, a wife, or even a close female-shaped pet sitter, which Dean finds susupicious as fuck. Dude’s hot as hell, has a good paying job, and, apart from his totally gag-worthy personality, has everything going for him. He’s gotta be hiding something else. Like a fetish for elbows or a ride-or-die thing for Jefferson Starship.

Dean turns around to face his brother, by now sporting a matching scowl. “He started it.”

“It’s Monopoly. Everyone starts shit Monopoly,” Sam says, crossing his arms over his chest. “Admit it, you have it out for Castiel. You always have.”

“So?” Dean sips angrily at his drink. “Dude needs to get that chip knocked off his shoulder.”

“What chip?” Sam asks, baffled. “He’s just an analyst at Charlie’s company. Dude’s fine.”

“He’s a dick,” Dean says stubbornly. “Thinks he’s too good to slum it with us at the bar at Happy Hour on Thursdays. It’s not like he’s going to get half priced drinks with anyone else working the joint.”

“He said he’s busy that day.”

“I don’t buy it,” Dean insists, “I bet he has a secret girlfriend on the side, or something, and he’s too ashamed of us to bring her. I told you, when I first met him, he asked me all these questions about my job, rubbing it in that I’m working behind a bar while he has a cushy office and a nine to five, never mind that I would blow my own fucking brains out than pull a Mad Men every day.”

“I’m pretty sure he was only trying to get to know you,” Sam says disapprovingly.

“So he can lord it over me how much better he has it.”

Sam throws him a pained look. “Dean, nobody but you thinks that about your job.”

Dean just tips back his (expertly made) old fashioned.

“If you ever wanted to try something different,” Sam says as he adds more soda to his rum and coke, “you know I would help you out. It wouldn’t be like last time.”

Dean shudders at the idea, and it’s only a little exaggerated. He’s no bloodsucker, leeching off his little brother. He didn’t bother Sam when he had nothing but six bucks in his bank account, a mortgage on a house he couldn’t stand to even look at anymore, and only his give ‘em hell attitude to keep him company. “I’ll stick with the booze, thanks.”

Sam throws him a pained look. “Just, don’t blow up at him, alright? This is supposed to be a party.”

**Hour -2**

“That’s it! I’m _done!”_ Dean declares, throwing down his two measly properties he managed to keep ahold of. “Take all my goddamn money.”

“Gladly,” Castiel says smugly as he adds Dean’s precious deeds to his pile.

Charlie slaps her hand against her forehead.

“Alright, it’s you and me angel boy,” Dorothy says, leaning across the board. “Bring it.”

**Hour -1**

Castiel’s face falls faster than Yoshi tumbles off Rainbow Road.

Dean’s currently holding the lead, but he’s not so distracted by his impending victory to miss Castiel epically fail at Mario Kart. Castiel hasn’t broken the top three since they started playing forty-five minutes ago, and Dean will cherish this moment forever.

“Oh, shut up,” Castiel grumbles as his eyes flick from the controller to the nearest wall and back again.

Dean’s gaze doesn’t deviate from the screen. “I didn’t say anything, jackass.”

“Oh my fucking god,” Sam mutters as he lobs a green koopa shell at Dean’s Mario.

Mario careens off the road as Luigi speeds past.

Dean’s mouth falls open as Lakitu gently sets Mario back on track. “What the hell, Sammy?” 

“All’s fair in love and war and Mario Kart,” Sam recites dutifully, his tongue between his teeth as he fights to keep his lead from Charlie’s Toad.

**Hour -0.5**

“Seriously, Dean?” Castiel demands over the sound of mashing buttons. “We are on the same team!”

“My bad,” Dean says blithely as he hammers on Yoshi again instead of aiming for Luigi or Toad. They’re clearly going to lose, but Dean might as well make it fun for himself.

Plus, there’s nothing Sam likes _less_ than playing a boring game of Super Smash Bros. Serves him right, for forcing Dean to be on a team with Castiel. _Oh we can’t be on a team together, Dean, we’ve had too much practice. It wouldn’t be fair_ \- Dean's ass.

Dean should’ve made Jo switch with him on the other console. He would have owned Garth and Kevin if he teamed up with Dorothy.

“You are being completely unreasonable,” Castiel grumbles.

“D’you know who whines, Cas?” Dean taunts as he bonks Luigi once in the head before wailing on Yoshi, “babies.”

Castiel bursts out, “Dammit, Dean!” as Yoshi gets blasted off screen, no thanks to Mario.

Dean isn’t the least bit sorry when Castiel finally throws his controller at the wall and storms into the kitchen for another glass of wine.

**Hour 0**

_“Give me those goddamn sheep!”_ Dean hollers as he brandishes three lumber cards and an ore in Castiel’s face. “I know you have ’em.”

“I might,” Castiel says calmly, “but that has no bearing on whether or not I wish to trade with you.”

“You need lumber for that road,” Dean reminds him testily.

“Dorothy has extra lumber she might be willing to trade me,” Castiel says, eyes narrowing.

Dorothy looks up from where she’d been whispering conspiratorially with Charlie. “Uh, Charlie just took my extra lumber. Sorry.”

Castiel glares daggers of betrayal at the pair of them. “I forfeit my turn,” he announces, crossing his arms across his chest like a toddler refusing to walk one more step further.

“Seriously?” Dean barks. “You’ve got to be kidding me.”

“I am not,” Castiel growls. “This whole evening, you’ve been recalcitrant and a poor loser. I don’t see why I have to accommodate such behavior.”

Dean slams down his hand on the table, rattling the game pieces ominously. “Of all the goddamn pretentious bullshit-”

“Woah,” Garth interrupts, alarmed. “Come on you guys, this doesn’t have to be a big deal-”

Dean cuts him off, “He made it a big deal when he refused to trade the sheep!”

Jo silently steals three ore cards from Sam while he’s staring at the action across the table and goes for a wheat card from Kevin. He slaps her hand away without even looking away.

“This is not about the sheep, and you know it, Dean Winchester,” Castiel says severely.

“Okay,” Charlie says loudly, her mouth set in a firm line. “Time out.”

“Yes, thank you,” Castiel says gratefully. “I could do with a break -”

“No, a time out, Charlie says, pointing unambiguously at Castiel and Dean, “You two, get out until you can play nice together.”

**Still Hour 0**

“Really?” Dean complains as Sam herds him and Castiel into the spare bedroom on the floor above. “You’re making me miss game night?”

“Wait.” Sam darts out of the room.

Dean shares a truly hateful glare with Castiel before looking around their prison, what appears to be the cabin's master bedroom. There's a queen sized bed in the middle of the room, decked out with a beige-and-tan pattered quilt. A dresser sits against the far wall, covered in pictures of the owners and knicknacks. Above the bed hangs a print of the cabin itself, depicted in Spring, with lots of green instead of the dead sticks Dean drove past on their way here. 

The lone window looks out onto the driveway, rapidly fading from view with the setting sun. The ledge below the window is padded with a matching beige-and-tan cushion. 

Sam returns carrying Connect 4. “Play this, if you have to.”

Dean grmaces. “Dude, that’s not what I-”

“You’re ruining Charlie’s birthday,” Sam hisses.

Dean barely holds back his flinch.

Off to the side, Castiel makes a face, but doesn’t disagree.

Sam runs a hand down his face. “Stay here. Cool off for a bit, okay?”

“With him?” Dean gasps, gesturing wildly.

“Jesus Christ, you’re so dramatic,” Sam mutters. “You don’t have to point.”

“You really don’t,” Castiel adds snidely, knocking Dean’s finger out of his face.

“Shut up.”

Castiel’s eyes flash. “Make me.”

Sam groans. “Yeah, you two… just do your thing up here - where we can’t hear the yelling.”

**Hour 0.5**

They’d been stuck in this room for almost thirty minutes, and Dean can feel the mind-numbing boredom creeping in like a rolling thundercloud. He’s lying on his back on the bed, trying not to fall asleep, since who knows what Castiel might draw on his face with that kind of access.

Castiel hasn’t said a word since Sam left. 

“Are you really not going to say anything?” Dean asks disparagingly to the ceiling. 

“I don’t think there’s anything to say,” Castiel mutters where he’s sitting by the window. He’s huddled in on himself, hugging his knees, and the pane has already frosted over from his breath. The guy probably can’t see shit, but he’s still looking out the window because he’s _also_ a dramatic bitch. And no one can convince Dean differently.

It’s only slightly past five in the evening, but the sun has already set. It’s dark as hell outside and souring Dean’s already crappy mood further. After running through and rejecting about a hundred things to ask, Dean eventually comes up with, “Aren’t you cold?”

Castiel throws him a confused look. “A little,” he admits to Dean’s surprise, “but there is nowhere else to sit.”

Dean purses his lips, the beginnings of guilt nipping at his heels. He’s sprawled all over the double bed in the center of the room while Castiel is confined to a freezing window seat built for some 18th century girl waiting to spot her father returning home from the war. In all honesty, Castiel looks cramped as shit, so Dean reluctantly sits up. “I guess the bed’s big enough.”

Castiel stares at him. “Are you serious?”

Dean shrugs. “Sam’s bitchface will freeze that way if he finds out I let you get frostbite or something.”

“It’s not nearly cold enough for that,” Castiel says even as he gets to his feet, hopping a little in place to shake the feeling back in his limbs.

Dean bristles. “Why, you the expert on frostbite?” he sneers, tapping his fingers against his thigh. He’d been in the bone-numbing cold before, the type of cold when each breath freezes in your chest and you have to keep shivering because if you don’t, something bad will happen. This… isn’t anything like that. But Dean’ll eat a Caesar salad, dressing on the side, before he admits any of that to Castiel Engel.

Castiel lifts his nose in the air. “No, that’s simply common sense.”

“I have common sense,” Dean retorts.

“Is that right?” Castiel asks imperiously. “So why do you drive a vehicle that has terrible gas mileage and, from what Charlie tells me, the most limited of safety features?”

Dean snaps.

Before his brain catches up with him, he’s on his feet and has Castiel pinned against the nearest wall, one arm braced across his chest to keep him in place. “Don’t you dare insult my baby,” he hisses.

“Your baby?” Castiel scoffs, his eyes widening as he takes in Dean’s face. They’re practically nose-to-nose.

“Yeah, she’s my fucking baby,” Dean says, digging in his heels like he always does when people insult the Impala. “You got a problem with that?”

“You do know it’s not sentient,” Castiel says like Dean is stupid.

 _“Sentient,”_ Dean says, mocking Castiel’s choice of words with everything he has, “or not, she’s been there for me when nobody else has, so you can fucking _lay off.”_ He lets Castiel go because, as angry as he is, he won’t deck the guy, and that’s his only other option in his position. “Christ,” he mutters as he paces to the other end of the too small bedroom, “I need a drink.”

Castiel, for once, doesn’t have anything to say in return.

As he calms down, breathing deep breaths, the faintest inklings of shame once again creep in. Castiel didn’t know he hit Dean’s sorest of sore spots. He was just being his usual bitchy self, and didn’t _really_ deserve Dean blowing up in his face like that. Dean should apologize. Or at least, try to make civil conversation.

Once he can finally bring himself to see what his time out partner is up to, he finds Castiel holding the Connect 4 box, a quizzical expression on his face. As if he feels the weight of Dean’s gaze on him, he looks up. “Would you like to play?”

Dean can recognize a peace offering when it’s on the table.

**Hour 1**

“What the hell?” Dean’s mouth falls open as he studies the perfect trap Castiel set up for him. Dean had won the past four games they’d played in rapid succession, with Castiel being a gracious loser for once. But this time, out of nowhere, Castiel swooped in and whooped his ass before Dean knew what hit him. 

Castiel smirks. “I’ll let you call it a tie, if you like.”

Dean raises his head above the Connect 4 grid, eyes narrowing in suspicion. “Were you _playing_ me?” he demands. “Letting me win?”

Castiel opens his mouth and closes it, and Dean can read the truth all over his face. But he doesn’t look smug or pleased with himself. If anything, he looks… guilty.

“Fine,” Dean grunts, undoing the latch that sends the pieces clattering back into the box. “No fucking tie. You win.”

Castiel smiles as he starts sorting his red pieces out from the black.

“This time,” Dean says emphatically, “No going easy. I mean it, Cas.”

“As you wish.”

Dean shoots him a look, but Cas is already contemplating his first move.

**Hour 1.5**

Right before Dean’s about to drop his piece and absolutely wreck Cas’s diagonal strategy, Cas asks, “If you don’t mind me asking, what did you mean earlier?”

“Huh?” Dean’s piece clacks into place.

Studying the board, Cas prompts without looking up, “About your car?”

“My baby?”

Cas nods solemnly. “Yes, your baby.”

“Oh,” Dean says, his face heating even though Sam and Charlie told him a hundred thousand times there’s nothing to be ashamed of. “I - well, I lived out of my car for a year or two a while back.”

“You did?” Cas asks, his face open and non-judgmental for once.

“Yeah,” Dean mutters, fiddling with a black piece. “Dad had just died without paying off the mortgage, and I couldn’t bother Sam since he was in his last year of law school, and then he was studying for the Bar, so… I just took off for a little while.”

“In your car?”

“Saw the biggest ball of twine like three times, which I don’t recommend,” Dean says with a humorless laugh.

Cas drops his next piece in the fourth column. “What did you do for income?”

“Took odd construction jobs or handyman gigs for a few weeks here and there,” Dean says, shrugging, “hustled pool when it got really tight.”

“When my father passed,” Cas says slowly, and Dean can’t tell if he’s waiting for Dean to tell him to shut up or trying to parse out the right words, “I drank a liquor store.”

“What?”

“My cousin, Gabriel, owns a liquor store slash adult video store slash fireworks depot, and he let me have free rein after my father’s funeral. I drank all his top shelf liquor and set him back approximately two thousand dollars.”

Dean whistles. “What’d you like the best?”

Cas shakes his head, smiling slightly. “Will you believe I don’t actually like hard liquor?”

Dean drums his fingers silently against the bedspread. As Cas plays his next move, Dean asks, “Is that why you never go to Happy Hour on Thursdays?”

“The taste of vodka makes me nauseated now,” Cas admits. “I can maybe stand one shot of whiskey before I have to excuse myself or vomit.”

Dean chuckles. “Y’know, you can always ask for a mocktail or something.”

Cas raises his eyebrows. “You already make fun of me for drinking wine.”

“I thought you were a wine snob!” Dean protests. “All the stuff you bring to Charlie’s is imported.”

Cas sighs. “After that incident, my cousin bought me a five year subscription to a wine of the month club.”

“They do that?” Dean asks, flat out horrified. “For five _years?”_

Cas’s expression sours. “Apparently very select clubs do. So far, I’ve successfully foisted off every bottle to Charlie.”

“Does your cousin know you don’t drink ‘em?”

Cas’s shoulders slump in defeat. “When I asked him to cancel the subscription, he renewed it for another year.”

Dean cracks up.

**Hour 2**

“I think we’ve played every single game of Connect 4,” Dean groans over the clatter of pieces as Cas resets the grid again. Dean lost, which somehow stings a little less each time.

“Considering there are approximately four trillion possible combinations, I doubt that,” Cas says mildly as he motions for Dean to go first.

“Whatever you say, smarty pants.”

Cas frowns. “I’m not a ‘smarty pants’. I was merely stating a fact.”

“Sure, but you don’t have to be all…” Dean struggles for the right word that won’t set him off. He winds up gesturing at Cas’s whole face. 

“I do not understand,” Cas says frankly.

Dean bites his lip. “’S just… sometimes… you kind of sound like a know-it-all.”

Cas frowns at that, be he doesn’t look angry, more contemplative. “Like Hermione?”

Dean nearly drops the token he’d been toying with. “You watched Harry Potter?” 

Cas’s missed references are practically legendary - not that Dean has been paying particular attention to Cas. It’s common knowledge, like never mention Advanced Placement classes around Kevin and don’t expect Cas to get any (hilarious) pop culture references.

“I read them, actually.”

Dean snorts. “Exactly like Hermione.”

One corner of Cas’s mouth lifts in a half-smile. “Charlie said I had to, or we couldn’t be friends.”

Dean snorts. “She said the same thing to me about LARPing.”

“I believe she’s working me up to that,” Cas says, leaning back on the bed as he waits for Dean to play his next piece. “But first, Harry Potter, Lord of the Rings, and maybe something about two brothers hunting the supernatural?”

“That’s for the best, dude,” Dean says as he drops his token in the grid. “LARP is a fucking blast, but I wouldn’t throw anyone into the craziness of nerd-dom with zero warning.”

Cas tilts his head, studying him intently. “You’re a nerd?”

“Come on,” Dean says, blushing bright red, “You saw me lose my shit over Mario.”

“I thought that was just your competitive side.”

“It can’t be both?” Dean asks defensively.

“But you never look particularly enthusiastic in Charlie’s Moondoor photos,” Cas points out.

“That’s my character! Spartacus the Stoic-” Dean explains as Cas chokes, “isn’t supposed to show emotion.”

“Spartacus?” Cas repeats with a straight face, but he’s clearly laughing on the inside.

“Shut up. It’s an awesome name.”

Cas contemplates his next move carefully, waiting until the red piece stops clattering to the bottom of the grid to say, “I thought you went to humor Charlie.”

“The first time, maybe,” Dean admits, “But not for a whole _year_. If you want to talk to someone who tried it and chickened out like a level one Shadow Orc, ask Sammy or _Emrys the Enchanter._ Talk about a stupid name.”

Cas makes a face. Opens his mouth. Closes it again.

“What?” Dean sighs. 

“I didn’t say anything.”

“Yeah, but you were thinking it. Come on, spit it out.”

Cas throws him a look that clearly says, _you asked for this._ “Emrys comes from the word immortal in Welsh. His name makes sense.”

Dean throws his hands in the air. “How the hell do you know that?”

Cas pinks. “I,” he falters, “I was very interested in King Arthur as a child. My father, after he came home from a long business trip in the UK, brought me back a book with the legends. I read it to pieces. Anyway, the name Emrys is associated with Merlin.”

“So Sammy was extra uncreative is what I’m hearing.”

“This coming from ‘Spartacus’.”

“Hey, it’s not like anyone actually calls my character that. Ever since Charlie said it was lame.”

“What do they call you instead?” Cas asks curiously. 

Dean mumbles the answer and regrets ever getting shut in this room with Castiel Engel. He plays his next move and tries not to sulk. 

“Excuse me?”

Dean sighs. He shouldn’t have even brought up LARPing. 

“Handmaiden,” he mutters. “Charlie made me her handmaiden on the first day so she could show me the ropes, and the title stuck, okay?”

Cas valiantly tries to hold in his laughter. 

Dean waves a stray hand. “Go on, yuk it up, you big mook.”

But Cas only grins and drops another red piece in the grid. “Connect 4,” he says. 

**Hour 2.5**

“So why you?”

“Why me what?” Cas asks absently as he deliberates between two columns for his next move.

“Why’re you friends with Charlie?” Dean asks. At Cas’s sharp look, he raises his hands in the air in a gesture of no-harm. “She doesn’t drag any of her other co-workers into our craziness.”

Cas purses his lips. After a long pause, he says in a low voice, “I think she felt sorry for me.”

 _“What?”_ Dean demands. “Why?”

Cas throws him an aggravated look. “Do I really need to elaborate?”

“Uh, yeah,” Dean fumbles, “’cause that makes less than zero sense.”

Cas grimaces like he just smelled Sam’s post-Chipotle farts. “She saw me reading coding manuals at lunch every day in the break room and intervened, apparently, to save me from myself.”

“But she loves coding,” Dean points out.

“And she could see I hated it,” Cas says plainly, to Dean’s complete surprise.

“Isn’t that your job?”

“Yes,” Cas says, lowering his head to study the grid again.

“I always thought you guys were nuts for working in cubicles all day.”

“I contemplate setting my desk on fire at least five times every day,” Cas says matter-of-factly. “Eight times, if we have all-hands meetings.”

Dean grins. “So enter Charlie?”

“Enter Charlie,” Castiel echoes. “One day, she just took my book and refused to give it back until I read her copy of Harry Potter.” He smiles wryly. “She said I could probably relate to Harry - a perpetual outsider who never feels at home in the world around him.”

Dean whistles. “Harsh.”

“But true,” Cas sighs as he plays his move.

Dean drops his token in without much thought. “I know there are probably a bunch of factors,” he says slowly, “but why don’t you quit? Do something else?”

Cas shrugs. “It’s all I’ve done since I graduated college. I don’t know how to do anything else.”

Dean bites his lip, watching Cas’s piece sink to the last open space in the bottom row. “I’ve done about every job under the sun that doesn’t require me to wear a monkey suit. I could give you a few pointers, if you’d like. You’re a smart guy. I’m sure there’s stuff that you could do that doesn’t make you want to blow your brains out.”

Cas smiles. “I’d like that.” He points to the neat little row of red circles, impossibly pleased after owning Dean’s ass for the approximate bajillionth time. “I connected four.”

For the first time, Dean could kiss that look off his face instead of (verbally) slapping it away.

_Son of a bitch._

**Hour 3**

Cas stretches, his spine popping and mouth pulling down into a pained grimace.

“You okay?”

“Yes,” Cas grumbles as he resumes his slouching position, all the better to see the board and wreck his back. “This is pretty mild compared to seven hours at my desk.” His gaze flicks up to Dean briefly before settling back on Connect 4 with his trademark intensity. “I used to envy you, you know.”

Struck dumb, Dean doesn’t answer until Cas plays his next move. “Why, dude?” he asks, dropping his piece into the next column over. “I’m just a bartender.”

Cas’s brow furrows. “That’s only your occupation. You are much more than that.”

Dean makes a face. “Not really.”

“I’m sure everyone downstairs would agree with me,” Cas says, a faint blush appearing on his cheeks. “From what I’ve heard, you are a good, reliable friend, Dean.”

“I - well, I helped a couple of people move, I guess, and I bring good booze to stuff. I didn’t donate a kidney or anything.”

Cas rolls his eyes. “Reliability rarely involves kidneys.” He presses his lips together, rubbing his thumb and forefinger along the side of one of his red pieces. After a long pause, he says, “Charlie told me about the year you lived on the road. She made it sound like you had no commitments, no responsibilities, like you were able to live your life on your own terms. I’ve never felt brave enough to do anything like that.”

“Yeah, well, she’s an incurable optimist,” Dean mutters. “Parts were great. Freezing my ass off in South Dakota when I was twenty bucks short for a night at the cheapest flea motel sucked balls.” He musters a weak smile. “Could’ve done with less twine too.”

“She didn’t mention your father either.”

“That’s for the best,” Dean snorts. “It really puts a damper on the whole free as a bird story.”

“I’m glad you told me.”

Dean shoots him a grin. “I’m glad we have equally shitty ways of coping with dead dads.”

“If I had a drink, I would toast to that,” Cas says, one corner of his mouth lifting up.

“When we get outta here, I’ll pour that first glass of wine myself.”

Cas smiles. “I would enjoy that very much.”

**Hour 3.5**

“Okay,” Dean says, pointing a finger straight at Cas’s face, “Once we’re out of this goddamn room, I’m going to give you a pop culture education. It’s a fucking crime that you don’t know the magic of Patrick Swayze.”

“Was he in Star Trek?”

Dean almost knocks over their Connect 4 game. “Are you seriously mixing up Patrick Stewart and Patrick Swayze? It’s Swayze, man!”

Cas pinks. “They are clearly very similar names.”

“Oh my god. I think I’m gonna be sick.”

Cas shoots him an exasperated look, saying, “I think Charlie is a big fan of Star Trek,” with the air of a train conductor switching tracks to avoid disaster.

“First Swayze,” Dean says seriously, “then Star Trek. There are a couple of series, and people argue about which one’s the best, but-”

Cas sighs. 

Dean plows on because Cas needs to know these things to be a functioning member of society, “-don’t let Charlie skip it. It’s cheesy as fuck but it’s a classic. No Deep Space Nine or The Next Generation until you know why Captain Kirk is the best captain of the USS Enterprise.”

“Charlie?” Cas echoes, confusion written all over his face before he drops his gaze to study Connect 4. 

“What about her?” Dean asks as he flips a token over his fingers.

“Nothing,” Cas says, averting his gaze, cagey has hell.

“Dude, come on.”

Cas releases a long sigh. “I was just under the impression we’d watch it together.”

Face warming, Dean plays his next move. “If you’d like that, sure,” he says, trying and mostly failing to keep his voice as casual as possible. He would have to dust his living room and grab a bottle of red from the bar, but he’s needed to clean for a while anyway. To distract himself from thinking too hard about having Cas over in his space, probably alone, in the dark, a couple drinks in, relaxed and open like he is tonight, he rambles, “I already have the whole original series on DVD, plus TNG, and I can totally borrow Next Gen from Kevin. D’you know, Kirk was the first dude I thought was hot? In one episode, he’s trapped on this desert planet, and his uniform’s all ripped…” Dean drifts off, grinning.

“For me, it was Errol Flynn,” Cas says as Dean’s mouth drops open. “I was watching Robin Hood with my mother, but then he came out in those tights.” Cas coughs, flushing. “It was a very embarrassing, enlightening experience.”

Silence reigns.

**Still Hour 3.5**

“I thought you were straight,” Dean says stupidly.

“I’m pansexual. None of Charlie’s friends are straight,” Cas says as he flips a red piece in his hand, analyzing the Connect 4 grid with a burning intensity usually reserved for high-stakes chess matches between the USA and USSR. 

“Yeah, but I thought -” Dean breaks off as Cas looks up at him, eyebrows raised. “I thought you were the token straight dude.”

“I was under the impression that was your brother.”

“Ha!” Dean almost goes for the third column but sinks his black token into the last column on the left at the last second. “So you admit it was possible.”

“I think Charlie lets him stay because he once kissed Ash on a dare and said, I quote, ‘that wasn’t so bad.’”

“Huh,” Dean says, frowning. “He didn’t tell me about that. Where was I?”

“You were attending a co-worker’s wedding in Oklahoma,” Cas says promptly. “You didn’t like them, but they promised an open bar and the ceremony was Western themed.”

Dean’s jaw drops open. “That was like a year and half ago.”

Cas’s face steadily reddens as Dean’s stunned silence drags on. “It’s your turn,” he mutters.

“I already went.”

“Oh, right,” Cas says, flustered, as he plays his next piece.

Dean plays his. “I connected four,” he says, but he can hardly concentrate on his win as the glorious implications of Cas’s unfortunate sexual awakening dawn on him.

Cas likes guys.

Cas might also be into guys who dress up in tights?

Okay, sure, Dean doesn’t wear tights to LARP, but his pants are still pretty small, and Cas already admitted he looked at pictures of Dean in his Handmaiden getup.

“Another game?” Cas asks loudly, breaking Dean’s concentration.

Dean jerks his head up to meet Cas’s anxious gaze. Slowly, he licks his lips.

Cas follows the movement of his tongue before snapping back up to his eyes. “Dean-” he starts, alarmed.

“No, I think I’m done with Connect 4,” Dean says, his voice low, as he leans in over the grid. “How ’bout you, Cas?”

“What else were you thinking we could do?” Cas asks warily, his baby blues wide.

“I was thinking we could make out for a bit,” Dean says in an absolutely bullshit casual voice, gesturing to the rest of the bed behind them, “and see where it goes from there.”

“Oh, thank god,” Cas mutters as he sweeps Connect 4 off the bed in a clatter of plastic chips.

They meet halfway.

**Hour 4**

The door opens. 

“Hey guys, so sorry we forgot about you for dinner - _holy shit, ow!”_ Sam hops on one foot, swearing at the floor. “Why are there pieces all over the,” he finally looks up, _“Oh - goddammit, gross!”_

Dean hastily grabs his shirt and checks to make sure his pants are still on - unzipped, but still holding up, despite Cas’s best efforts. He glances over at Cas, whose hair is sticking up like he stuck his fingers in an electrical socket and not down the waistband of Dean’s jeans. 

Sam slaps his hand over his eyes. “You guys!”

Dean sits up, glaring. “You locked us in here. There’s only so many games of Connect 4 a man can take, Sammy.”

“We played seventy two,” Cas adds gravely. “I think we gave it our best effort.”

Dean nudges him with his elbow. “Damn right we did.”

“Oh my god!” Charlie squeals behind Sam as she skids to a stop outside their door. “You _guys!”_

“I can’t believe you,” Sam says, jumping out of the way as Charlie elbows further into the room.

“I can,” Charlie declares, grinning up at him. “They were stuck in here while we were all having fun downstairs. What did you think would happen?”

“Murder?” Sam suggests, “A broken bone or two?”

“Hey, Cas,” Dean waggles his eyebrows, “I can help you out with a _bone-”_

“Dean!” Sam says, clearly pained, as Charlie cackles. “Look, I came up here to see if you were hungry. We just finished dinner.”

Dean tugs his flannel on and gets to work buttoning up Cas’s shirt, knocking Cas’s hands out of the way when he tries to do it himself. “Fix your hair,” he mutters.

Cas obediently runs his hands over his scalp, smoothing down the worst of it. His flushed cheeks and broad smile still give game away, though, which Dean doesn’t mind so much.

As Dean gets to work making himself presentable, Sam asks, “Were you seriously making out the whole time?”

“Not all of it,” Dean says defensively. “We did play an assload of Connect 4.”

“So, successful game night?” Charlie asks as she bends down to pick up the pieces still scattered by the bed. 

Cas hops down to help put everything away. “I’d say so,” he says in a low voice.

“Would’ve been more successful if we didn’t get _interrupted_ by a wild Samsquatch,” Dean grumbles above them.

“I thought you’d be crawling the walls by now,” Sam says, crossing his arms over his chest. “I know how you get when you’re hungry, Dean.”

Dean grins. “You know what’s the next best thing when you’re hungry?”

Sam grimaces. “No, and I don’t want-”

 _“Orgasms,”_ Dean interrupts smugly as Sam groans out loud. “So, what d’you say, Cas?”

Sam makes a disgusted noise in the back of his throat.

“I’m not a fan of voyeurism,” Cas says primly, dropping the last of the Connect 4 pieces in the box.

Dean waves Sam away as he sidles closer to Cas. “How big is the sleeping bag you brought for the slumber party part, anyway?”

Cas eyes him up and down. “Not big enough for two grown men.”

“Thank god,” Sam mutters, adding pointedly, “Neither is yours, Dean.”

“This bedroom’s going to be free, though,” Charlie says cheerfully, “since everyone else is going to be sleeping on the ground floor.”

“Ha!” Dean says triumphantly, raising a hand to high-five Charlie. “That’s why you’re my best wingwoman, and you,” he says with a glare at Sam, “are the worst little brother ever. Cas?”

Almost on his way downstairs, Cas turns in the doorway. “Yes, Dean?”

“I’ll get you a glass of wine if you’ll save me a spot?” he offers.

Cas smirks. “As you wish,” he says as he leaves.

Charlie nudges Dean in the side with her elbow, hissing, “You know I made him watch the Princess Bride last week, right?”

Sam spends way too long laughing at Dean’s bright red face, so Dean has no choice but to wallop him with a pillow and go track down Cas. He has some wine to deliver, after all.

**Author's Note:**

> This fic is also rebloggable on [tumblr!](https://goldenraeofsun.tumblr.com/post/643926928802430976/playing-nice)


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